Brom Bones tells Ichabod Crane the story of the Headless Horseman, who lost his head long ago during the Revolutionary War. Every Halloween night he rides in Sleepy Hollow looking for a new head. The best way to escape him is to cross the bridge, as the Horseman's dark powers are limited only to the woods.
That very night, Ichabod rides home alone and keeps imagining that he is being followed. When he finds that it's only cattails bumping on a log, Ichabod and his horse hysterically laugh, but suddenly stop as another laugh joins them. They both slowly turn around to find the Headless Horseman about to attack them, sword at the ready. He gives chase, laughing all the while. When Ichabod momentarily is trapped on the Horseman's own black steed, he looks down the Horseman's neck to find nothing but evil hollow laughter. Ichabod runs for the bridge and barely manages to make it across. As Ichabod turns around, he screams as the black horse rears up and the Headless Horseman throws a flaming jack o' lantern right at him.
The very next morning, Ichabod's hat was found next to a shattered pumpkin. However, Ichabod had vanished. Rumors about Ichabod still alive and married to a wealthy widow in a distant county are all but dismissed, as the good townsfolk of Sleepy Hollow know that he must have been spirited away (most likely killed) by the Headless Horseman himself.
The Headless Horseman appears in House of Mouse, as a recurring guest in the audience.
The Headless Horseman is briefly mentioned by the King, who says he once displeased him, and subsequently "lost his head", implying that the Horseman was beheaded on order of the King.
The Headless Horseman is part of various Halloween festivities at Walt Disney World, leading the Boo to You Parade at Mickey's Not So Scary Halloween Party and being the center of a Sleepy Hollow themed haunted hayride at Fort Wilderness.
At Hong Kong Disneyland, the Headless Horseman was the host of the 2011 Halloween festivities. He lead the Halloween parade and starred in a new haunted maze in Adventureland, The Revenge of the Headless Horseman. Here, a member of an Adventurers Club has claimed to have found his head and is presenting it in a sideshow exhibit, provoking the Horseman's wrath. This attraction proved popular enough to become a recurring feature of the event.
The Horseman also has a spell card known as "The Headless Horseman's Exploding Jack-O-Lantern" in the attraction Sorcerers of the Magic Kingdom.
- It is unknown whether or not the Headless Horseman was a real phantom or Brom Bones in disguise (as it was heavily implied in the book that the movie was based on). However, there are some suggestions that the Horseman was indeed an actual phantom, though from what was shown of Ichabod's fearful imagination beforehand, some of these things may have just been imagined by him:
- Ichabod had looked inside his cloak, seeing nothing there.
- Brom's horse did not have red eyes and a black mane like the Horseman's did.
- Brom needed a saddle, reins, and a bridle to ride his horse, while the Horseman apparently didn't. His implied spiritual nature would likely allow him to remain on his horse without any real support.
- The Horseman appeared to be slightly skinnier than Brom.
- The Horseman pulled his fiery pumpkin head out of nowhere when he threw it at Ichabod, almost is though it were by magic.
- In many early versions of the Haunted Mansion, the Headless Horseman was to be a focal point of the attraction's graveyard climax.
- A portrait of the Headless Horseman can be see in the video game Epic Mickey; in Lonesome Manor's library.
- The Headless Horseman is actually one of the very few Disney Villains to actually "win" rather than being defeated at the end of his/her film.
- Despite making a small appearance, the Headless Horseman is considered one of the darkest and most disturbing Disney villains.
- The Headless Horseman appeared on the Wonderful World of Disney the same Sunday night that The Beatles were on The Ed Sullivan Show.